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Synthesis of Novel Iminosugar‐Based Trehalase Inhibitors by Cross‐Metathesis Reactions
Author(s) -
Bini Davide,
Forcella Matilde,
Cipolla Laura,
Fusi Paola,
Matassini Camilla,
Cardona Francesca
Publication year - 2011
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201100484
Subject(s) - chemistry , trehalase , iminosugar , metathesis , hydrogenolysis , salt metathesis reaction , catalysis , combinatorial chemistry , stereochemistry , carbene , organic chemistry , enzyme , polymerization , polymer
The synthesis of a novel class of trehalase inhibitors composed of iminopyranose or iminofuranose residues linked at the pseudoanomeric carbon through an alkyl chain is described. A set of six novel compounds was prepared by the same reaction sequence involving the Grubbs Ru–carbene‐catalyzed cross‐metathesis (CM) of different N ‐Cbz‐protected allyl C ‐iminoglycosides as the key step in homo‐ or heterodimerization reactions. The target products, obtained with the CM reaction, were fully hydrogenated by catalytic hydrogenolysis, and preliminary biological screening of the products as inhibitors of commercially available porcine trehalase was performed.